4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester
• CAS No.: 129354-33-2
• Molecular Formula: C₅₀H₅₇NO₁₀Si₂
• Molecular Weight: 888.174

Synonyms:4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester

Chemical Property of 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester

Chemical Property:

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Technology Process of 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester

There total 8 articles about 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

Acetic acid (2R,3R,4S,5S)-5-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-tetrahydro-pyran-3-yl ester (129354-10-5,129354-32-1) + 4-nitro-benzoyl chloride (122-04-3) → 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester (129354-33-2)

Guidance literature:

With pyridine; at 20 ℃; for 20h;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

2,2,2-trichloroethyl 4,6-O-isopropylidene-α-D-mannopyranoside (128376-94-3) → 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester (129354-33-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / imidazole / dimethylformamide / 48 h

2: 45 percent / KH, Bu₄NI / dimethylformamide / 16 h / 20 °C

3: 96 percent / 70percent aq. AcOH / 1 h / 70 °C

4: imidazole / dimethylformamide / 24 h / 20 °C

5: 82 percent / pyridine / 16 h / 20 °C

6: 60 percent / Zn, AcOH / tetrahydrofuran / 1.) 16 h, 20 deg C 2.) 15 h, 20 deg C

7: 83 percent / pyridine / 20 h / 20 °C

With pyridine; 1H-imidazole; tetra-(n-butyl)ammonium iodide; potassium hydride; acetic acid; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

2,2,2-trichloroethyl 3-O-tert-butyldiphenylsilyl-4,6-O-isopropylidene-α-D-mannopyranoside (129354-05-8) → 4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester (129354-33-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 45 percent / KH, Bu₄NI / dimethylformamide / 16 h / 20 °C

2: 96 percent / 70percent aq. AcOH / 1 h / 70 °C

3: imidazole / dimethylformamide / 24 h / 20 °C

4: 82 percent / pyridine / 16 h / 20 °C

5: 60 percent / Zn, AcOH / tetrahydrofuran / 1.) 16 h, 20 deg C 2.) 15 h, 20 deg C

6: 83 percent / pyridine / 20 h / 20 °C

With pyridine; 1H-imidazole; tetra-(n-butyl)ammonium iodide; potassium hydride; acetic acid; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84222-G

upstream raw materials:

Acetic acid (2R,3R,4S,5S)-5-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-tetrahydro-pyran-3-yl ester

4-nitro-benzoyl chloride

2,2,2-trichloroethyl 4,6-O-isopropylidene-α-D-mannopyranoside

2,2,2-trichloroethyl 3-O-tert-butyldiphenylsilyl-4,6-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

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